KR20200121228A - An organic compound and an organic light emitting diode - Google Patents

Abstract

The present invention relates to a novel organic compound and an organic light-emitting device comprising the same and, more specifically, to an organic compound having excellent longevity, efficiency, electrochemical stability, and thermal stability, and an organic electroluminescent device comprising the same. The compound can be represented by chemical formula 1 or chemical formula 2.

Description

An organic compound and an organic light emitting diode comprising the same

The present invention relates to a novel organic compound and an organic electroluminescent device including the same.

The organic electroluminescent device (OLED) has a simple structure and various advantages in the manufacturing process compared to other flat panel display devices such as conventional liquid crystal display devices (LCD), plasma display panels (PDP), and field emission displays (FED). High luminance and viewing angle characteristics are excellent, response speed is fast, and driving voltage is low, so it is actively developed and commercialized to be used as a light source for flat panel displays such as wall-mounted TVs or backlights of displays, lighting, and billboards.

The first organic EL device was reported (CW Tang, SA Vanslyke, Applied Physics Letters, Vol. 51, 913 pages, 1987) by Eastman Kodak's CW Tang and others. When a voltage is applied, holes injected from the anode and electrons injected from the cathode recombine to form an electron-hole pair of excitons, which are converted into light by transferring the energy of the excitons to the light emitting material.

More specifically, the organic electroluminescent device has a structure including a cathode (electron injection electrode) and an anode (hole injection electrode), and at least one organic layer between the two electrodes. At this time, the organic electroluminescent device is a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL) or an electron from the anode. It is stacked in the order of an electron injection layer (EIL), and an electron blocking layer (EBL) or a hole blocking layer (HBL) is added to the front and back of the emission layer to increase the efficiency of the emission layer. Can be included as.

As the material used in the organic layer of the organic electroluminescent device, pure organic materials or complex compounds in which organic materials and metals form a complex account for most. Depending on the use, hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electrons It can be classified into injection materials.

Here, as a hole injection material or a hole transport material, an organic material that is easily oxidized and has an electrochemically stable state upon oxidation is mainly used. As an electron injection material or an electron transport material, an organic material that is easily reduced and has an electrochemically stable state upon reduction is mainly used.

Meanwhile, a material having a stable form in both oxidized and reduced states is preferable as the material of the emission layer, and a material having high luminous efficiency that converts excitons into light when formed is preferable. More specifically, the light emitting layer is composed of two materials, a host and a dopant, and the dopant must have high quantum efficiency, and the host material has an energy gap larger than that of the dopant material so that energy transfer to the dopant can easily occur. It is desirable. Displays used in TVs and mobiles are red, green, and blue in full color, respectively, and the emitting layer is composed of red host/dopant, green host/dopant, and blue host/dopant, respectively. Is composed.

Materials used as conventional blue dopants accounted for a large proportion of the use of fluorescent molecules such as Perylene, Comarin, Anthracene, and Pyrene, but the emission spectrum and full width of the dopant As the width half the maximum) is wide, there is a disadvantage that pure blue light cannot be used when manufacturing a device. This characteristic is the main reason not only to reduce the efficiency of blue in the resonance structure of the device, but also to make it difficult to utilize the deep blue section.

Recently, a document using a boron-based dopant having a narrow emission spectrum and high device efficiency is published in Adv. Mater. 2016, 28, 2777-2781 and Angew. Chem. Int. It was published in Ed 2017, 56, 5087-5090 and disclosed in Korean Laid-Open Patent Publication No. 10-2016-0119683. In the case of the previously introduced boron-based blue dopant material, boron atoms are included in the center and are cyclized. As a result, the structure of the molecule is maintained in a plane state as boron forms only a tri-coordinate bond.

Such a planar dopant has an advantage of being able to emit pure light because the energy level of the vibration mode of the molecule is similar, and the emission spectrum and the half width are narrowed.

(Non-Patent Document 1) Krebs, Frederik C., et al. "Synthesis, Structure, and Properties of 4, 8, 12- Trioxa-12c-phospha-4, 8, 12, 12c-tetrahydrodibenzo [cd, mn] pyrene, a Molecular Pyroelectric." Journal of the American Chemical Society 119.6 (1997): 1208-1216.

An object of the present invention is to provide a novel organic compound and an organic electroluminescent device including the same.

Another object of the present invention is to provide a novel compound that has a narrow emission spectrum and half width and can be used as an organic compound as a material for a light emitting layer, a hole injection layer, a hole transport layer, or an electron blocking layer.

Another object of the present invention is to provide an organic electroluminescent device having a low driving voltage and particularly excellent characteristics such as life, using an organic compound having excellent lifespan, efficiency, electrochemical stability, and thermal stability.

Another object of the present invention is to provide a blue host/dopant system and an organic electroluminescent device suitable for AM-OLED by using the organic compound.

In order to achieve the above object, the present invention provides a compound represented by the following Formula 1 or Formula 2, or a multimer compound including the structure of the compound represented by the following Formula 1 or Formula 2:

[Formula 1]

[Formula 2]

here,

n is an integer from 0 to 2,

1이고,a to f are the same as or different from each other, each independently an integer of 0 or 1, a + b + c + d

Is 1,

1이고,e + f

Is 1,

Y ₁ and Y ₂ are the same as or different from each other, and each independently B, N, P=O or P=S,

Rings A to G are the same or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms,

X ₁ to X ₃ are the same as or different from each other, and each independently B, N, O, S, Se or Si,

X ₄ is B, O, S, NR ₃ , Si(R ₄ )(R ₅ ) or Se,

Z ₁ to Z ₆ are the same as or different from each other, and each independently Si(R ₆ )(R ₇ ), B(R ₈ ), N(R ₉ ), a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, It is selected from the group consisting of a substituted or unsubstituted alkenylene group having 2 to 10 carbon atoms and a substituted or unsubstituted arylene group having 6 to 30 carbon atoms,

R ₁ to R ₉ are the same as or different from each other, and each independently hydrogen, a cyano group, a trifluoromethyl group, a nitro group, a halogen group, a hydroxy group, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, A substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C20 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C24 alkynyl group , Substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, substituted or unsubstituted 6 to 30 carbon atoms Heteroarylalkyl group, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, substituted or unsubstituted carbon number 6 to 30 aralkylamino group, substituted or unsubstituted C2-C24 hetero arylamino group, substituted or unsubstituted C1-C30 alkylsilyl group, substituted or unsubstituted C6-C30 arylsilyl group, and It is selected from the group consisting of a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and may be bonded to each other with adjacent groups to form a substituted or unsubstituted ring,

When A to G, Z ₁ to Z ₆ and R ₁ to R ₉ are substituted, hydrogen, cyano group, trifluoromethyl group, nitro group, halogen group, hydroxy group, alkylthio group having 1 to 4 carbon atoms, 1 carbon number Alkyl group of to 30, cycloalkyl group of 1 to 20 carbon atoms, alkenyl group of 2 to 30 carbon atoms, alkynyl group of 2 to 24 carbon atoms, aralkyl group of 7 to 30 carbon atoms, aryl group of 6 to 30 carbon atoms, 2 to 60 carbon atoms Heteroaryl group, heteroarylalkyl group having 6 to 30 carbon atoms, alkoxy group having 1 to 30 carbon atoms, alkylamino group having 1 to 30 carbon atoms, arylamino group having 6 to 30 carbon atoms, aralkylamino group having 6 to 30 carbon atoms, 2 to 24 carbon atoms Is substituted with a substituent selected from the group consisting of a heteroarylamino group, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms, and is bonded to adjacent groups to be substituted or provided A cyclic ring may be formed, and when substituted with a plurality of substituents, they are the same as or different from each other.

In addition, the present invention is a first electrode; A second electrode provided opposite to the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the one or more organic material layers is a compound represented by Formula 1 or 2, or Formula 1 or It provides an organic electroluminescent device comprising a compound that is a multimer including the structure of the compound represented by Formula 2.

For example, the organic electroluminescent device may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like. However, the structure of the organic electroluminescent device is not limited thereto, and may include a smaller number of organic material layers.

According to a preferred embodiment of the present invention, the organic material layer is an emission layer, and the emission layer comprises a compound represented by Chemical Formula 1 or Chemical Formula 2, or a multimer compound including a structure of a compound represented by Chemical Formula 1 or Chemical Formula 2. It may be characterized by including.

According to a preferred embodiment of the present invention, the organic material layer is a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, a hole transport layer, or an electron blocking layer is a compound represented by Formula 1 or Formula 2, or the It may be characterized by including a compound that is a multimer including the structure of the compound represented by Formula 1 or Formula 2.

In the present invention, "hydrogen" is hydrogen, light hydrogen, deuterium or tritium.

In the present specification, “halogen group” is fluorine, chlorine, bromine or iodine.

In the present invention, “alkyl” refers to a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.

In the present invention, "alkenyl" refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include vinyl (vinyl), allyl (allyl), isopropenyl (isopropenyl), 2-butenyl (2-butenyl), and the like, but is not limited thereto.

In the present invention, “alkynyl” refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.

In the present invention, "alkylthio" refers to the above-described alkyl group bonded through a sulfur linkage (-S-).

In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. In addition, a form in which two or more rings are simply attached to each other or condensed may be included. Examples of such aryl include phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and dimethylfluorenyl, but are not limited thereto.

In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 6 to 30 carbon atoms. At this time, one or more carbons, preferably 1 to 3 carbons in the ring are substituted with heteroatoms such as N, O, S or Se. In addition, a form in which two or more rings are simply attached to each other or condensed may be included, and further, a form condensed with an aryl group may be included. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, phenoxathienyl, indolizinyl, indolyl ( indolyl), purinyl, quinolyl, benzothiazole, polycyclic rings such as carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, “aryloxy” is a monovalent substituent represented by RO-, and R means an aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R'refers to alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure It may include. Examples of the alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.

In the present invention, "alkoxy" may be a straight chain, branched chain or cyclic chain. Although the number of carbon atoms of the alkoxy is not particularly limited, it is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. May be, but is not limited thereto.

In the present invention, "aralkyl" refers to an aryl-alkyl group in which aryl and alkyl are as described above. Preferred aralkyls include lower alkyl groups. Non-limiting examples of suitable aralkyl groups include benzyl, 2-phenethyl and naphthalenylmethyl. Bonding to the parent moiety is made through alkyl.

In the present invention, "arylamino group" refers to an amine substituted with an aryl group having 6 to 30 carbon atoms.

In the present invention, "alkylamino group" means an amine substituted with an alkyl group having 1 to 30 carbon atoms.

In the present invention, "aralkylamino group" refers to an amine substituted with an aryl-alkyl group having 6 to 30 carbon atoms.

In the present invention, "heteroarylamino group" refers to an aryl group having 6 to 30 carbon atoms and an amine group substituted with a heterocyclic group.

In the present invention, "heteroaralkyl group" refers to an aryl-alkyl group substituted with a heterocyclic group.

In the present invention, “cycloalkyl” refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, but are not limited thereto.

In the present invention, "heterocycloalkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 carbon atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S or Se Is substituted with a hetero atom such as. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.

In the present invention, “alkylsilyl” refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and “arylsilyl” refers to silyl substituted with aryl having 6 to 60 carbon atoms.

In the present invention, "condensed ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

In the present invention, 　“adjacent 　 groups are bonded to each other to form a ring” means 　adjacent 　 groups are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aliphatic heterocycle; Substituted or unsubstituted aromatic heterocycle; Or it means to form a condensed ring of these.

In the present specification, “alicyclic compound” has the same meaning as “aliphatic hydrocarbon ring”, and refers to a ring consisting of only carbon and hydrogen atoms as a non-aromatic ring.

In the present specification, “hetero-alicyclic compound” refers to an alicyclic compound including at least one heteroatom by substitution of one or more carbons of the “aliphatic hydrocarbon ring” with a hetero atom.

In the present specification, examples of the "aromatic hydrocarbon ring" include a phenyl group, a naphthyl group, an anthracenyl group, and the like, but are not limited thereto.

In the present specification, "aliphatic heterocycle" refers to an aliphatic ring including one or more of heteroatoms.

In the present specification, "aromatic heterocycle" refers to an aromatic ring including at least one heteroatom.

In the present specification, an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, an aliphatic heterocycle, and an aromatic heterocycle may be monocyclic or polycyclic.

In the present specification, “concentration quenching” means that the luminous efficiency of the device decreases as the concentration of the dopant molecule increases.

In the present specification, the terms "boron-based element", "boron-based compound", and "boron-based dopant" mean a boron (B) element having an atomic number of 5, a compound containing boron, or a dopant.

In the present specification, "substitution" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other. The substituent is hydrogen, cyano group, nitro group, halogen group, hydroxy group, alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 30 carbon atoms, alkynyl group having 2 to 24 carbon atoms, heteroalkyl group having 2 to 30 carbon atoms, 6 to carbon atoms 30 aralkyl group, C5 to C30 aryl group, C2 to C30 heteroaryl group, C3 to C30 heteroarylalkyl group, C1 to C30 alkoxy group, C1 to C30 alkylamino group, C6 to C6 It may be substituted with one or more substituents selected from the group consisting of an arylamino group of 30, an aralkylamino group having 6 to 30 carbon atoms, and a hetero arylamino group having 2 to 24 carbon atoms, but is not limited to the above examples.

The present invention provides a novel compound that can be used as a material for a light emitting layer, a hole injection layer, a hole transport layer, or an electron blocking layer as an organic compound having a narrow emission spectrum and half width.

The present invention provides an organic electroluminescent device having a low driving voltage and particularly excellent lifespan, by using an organic compound having excellent lifespan, efficiency, electrochemical stability, and thermal stability.

In addition, the present invention provides a blue host/dopant system and an organic electroluminescent device suitable for AM-OLED using the organic compound.

Hereinafter, embodiments of the present invention will be described in detail so that those skilled in the art can easily implement the present invention. However, the present invention may be implemented in various different forms and is not limited to the embodiments described herein.

The organic compound according to the present invention has a planar structure and minimizes the mutual attraction of the molecules in the molecule pi (π -π), while the energy level of the vibration mode of the molecule is almost similar, so a narrow emission spectrum And it characterized in that it has a half width.

The organic compound according to the present invention, including atoms that provide a planar structure, such as boron-based elements, interferes with the formation of excitable dimers in the molecule, and increases the electron density of the core and the stability of the dopant, thereby increasing the efficiency and life of the device. Can be made possible.

Specifically, a compound represented by the following Formula 1 or Formula 2, or a multimer compound including the structure of the compound represented by the following Formula 1 or Formula 2 is as follows:

[Formula 1]

[Formula 2]

here,

n is an integer from 0 to 2,

1이고,a to f are the same as or different from each other, each independently an integer of 0 or 1, a + b + c + d

Is 1,

1이고,e + f

Is 1,

Y ₁ and Y ₂ are the same as or different from each other, and each independently B, N, P=O or P=S,

Rings A to G are the same or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms,

X ₁ to X ₃ are the same as or different from each other, and each independently B, N, O, S, Se or Si,

X ₄ is B, O, S, NR ₃ , Si(R ₄ )(R ₅ ) or Se,

Z ₁ to Z ₆ are the same as or different from each other, and each independently Si(R ₆ )(R ₇ ), B(R ₈ ), N(R ₉ ), a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, It is selected from the group consisting of a substituted or unsubstituted alkenylene group having 2 to 10 carbon atoms and a substituted or unsubstituted arylene group having 6 to 30 carbon atoms,

R ₁ to R ₉ are the same as or different from each other, and each independently hydrogen, a cyano group, a trifluoromethyl group, a nitro group, a halogen group, a hydroxy group, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, A substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C20 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C24 alkynyl group , Substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, substituted or unsubstituted 6 to 30 carbon atoms Heteroarylalkyl group, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, substituted or unsubstituted carbon number 6 to 30 aralkylamino group, substituted or unsubstituted C2-C24 hetero arylamino group, substituted or unsubstituted C1-C30 alkylsilyl group, substituted or unsubstituted C6-C30 arylsilyl group, and It is selected from the group consisting of a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and may be bonded to each other with adjacent groups to form a substituted or unsubstituted ring,

When A to G, Z ₁ to Z ₆ and R ₁ to R ₉ are substituted, hydrogen, cyano group, trifluoromethyl group, nitro group, halogen group, hydroxy group, alkylthio group having 1 to 4 carbon atoms, 1 carbon number Alkyl group of to 30, cycloalkyl group of 1 to 20 carbon atoms, alkenyl group of 2 to 30 carbon atoms, alkynyl group of 2 to 24 carbon atoms, aralkyl group of 7 to 30 carbon atoms, aryl group of 6 to 30 carbon atoms, 2 to 60 carbon atoms Heteroaryl group, heteroarylalkyl group having 6 to 30 carbon atoms, alkoxy group having 1 to 30 carbon atoms, alkylamino group having 1 to 30 carbon atoms, arylamino group having 6 to 30 carbon atoms, aralkylamino group having 6 to 30 carbon atoms, 2 to 24 carbon atoms Is substituted with a substituent selected from the group consisting of a heteroarylamino group, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms, and is bonded to adjacent groups to be substituted or provided A cyclic ring may be formed, and when substituted with a plurality of substituents, they are the same as or different from each other.

Preferably, the compound may be a compound selected from the group consisting of a compound represented by Formula 1, a compound represented by Formula 2, and a compound in which a unit structure represented by Formula 1 or Formula 2 is condensed. .

The rings A to G may be the same or different from each other, and each independently a substituted or unsubstituted aryl group having 5 to 15 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.

The compound may be a compound selected from the group consisting of a compound represented by the following Formula 3 or Formula 4, or a compound in which the unit structure represented by the following Formula 3 or Formula 4 is condensed:

[Formula 3]

[Formula 4]

here,

n, a, b, c, d, e, f, Y ₁ , Y ₂ , X ₁ to X ₄ , Z ₁ to Z ₆ , R ₁ and R ₂ are as defined in claim 1,

m, p, q, r and u are the same as or different from each other, and each independently an integer of 0 to 3,

t is an integer from 0 to 4,

R ₁₀ to R ₁₆ are the same as or different from each other, and each independently hydrogen, a cyano group, a trifluoromethyl group, a nitro group, a halogen group, a hydroxy group, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, A substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C20 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C24 alkynyl group , Substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, substituted or unsubstituted 6 to 30 carbon atoms Heteroarylalkyl group, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, substituted or unsubstituted carbon number 6 to 30 aralkylamino group, substituted or unsubstituted C2-C24 hetero arylamino group, substituted or unsubstituted C1-C30 alkylsilyl group, substituted or unsubstituted C6-C30 arylsilyl group, and It is selected from the group consisting of a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and may be bonded to each other with adjacent groups to form a substituted or unsubstituted ring,

When the R ₁₀ to R ₁₆ are substituted, hydrogen, cyano group, trifluoromethyl group, nitro group, halogen group, hydroxy group, alkylthio group having 1 to 4 carbon atoms, alkyl group having 1 to 30 carbon atoms, having 1 to 20 carbon atoms A cycloalkyl group, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, a heteroaryl group having 6 to 30 carbon atoms Arylalkyl group, C1 to C30 alkoxy group, C1 to C30 alkylamino group, C6 to C30 arylamino group, C6 to C30 aralkylamino group, C2 to C24 heteroarylamino group, C1 to C30 It is substituted with a substituent selected from the group consisting of an alkylsilyl group, an arylsilyl group having 6 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms, and may be combined with adjacent groups to form a substituted or unsubstituted ring. When substituted with four substituents, they are the same as or different from each other.

The compound in which the unit structure represented by Formula 1 or Formula 2 is condensed or the form in which the unit structure represented by Formula 3 or Formula 4 is condensed is a form in which a cyclic compound contained in the unit structure is shared so as to be bonded to each other, It is a form in which the rings of the ring included in the unit structure are condensed to each other.

The form of the condensation compound may be a compound in which the unit structure is condensed as shown in the following example, but may include a range that is apparent by a person skilled in the art:

The Y ₁ and Y ₂ may be B.

The X ₁ to X ₃ may be the same as or different from each other, and may each independently be N or O.

The compound represented by Formula 1 or Formula 2 according to the present invention may be represented by the following compounds, but is not limited thereto:

The compound of Formula 1 or Formula 2 of the present invention may be usefully used as a dopant material for a light emitting layer. Specifically, the organic compound is a dopant material and may provide an organic compound that is thermally stable compared to a conventional boron-based dopant.

The organic compound of the present invention can be usefully used as a material for forming a light emitting layer. In the above, the material for forming the light-emitting layer may further include a material commonly added when the organic compound is manufactured in a form necessary for use in forming the light-emitting layer, such as a host material.

The material for forming the light emitting layer may be a material for a dopant.

The present invention provides an organic electroluminescent device comprising a compound represented by Formula 1 or Formula 2, or a multimer compound including a structure of the compound represented by Formula 1 or Formula 2.

The organic compound of the present invention can be usefully used as a material for forming a hole injection layer, a hole transport layer, or an electron blocking layer.

In addition, the present invention relates to a material for forming a light emitting layer containing the organic compound.

In the above, the material for forming the light-emitting layer may further include a material commonly added when the organic compound is manufactured in a form necessary for use in forming the light-emitting layer, such as a host material.

In addition, the present invention is an organic electroluminescent device in which an organic thin film layer comprising at least one layer or a plurality of layers including a light emitting layer is stacked between a cathode and an anode,

It relates to an organic electroluminescent device, characterized in that the light-emitting layer contains the organic compound represented by the formula (1) or (2) alone or in combination of two or more.

The organic electroluminescent device may have a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are stacked, and an electron blocking layer, a hole blocking layer, etc. are additionally stacked if necessary. Can be.

Hereinafter, the organic electroluminescent device of the present invention will be described by way of example. However, the contents illustrated below do not limit the organic electroluminescent device of the present invention.

The organic electroluminescent device of the present invention may have a structure in which an anode (hole injection electrode), a hole injection layer (HIL), a hole transport layer (HTL), an emission layer (EML), and a cathode (electron injection electrode) are sequentially stacked, Preferably, an electron blocking layer (EBL) between the anode and the emission layer, and an electron transport layer (ETL) and an electron injection layer (EIL) between the cathode and the emission layer may be further included. In addition, a hole blocking layer (HBL) may be further included between the cathode and the emission layer.

In the method of manufacturing an organic light emitting diode according to the present invention, first, an anode is formed by coating a material for an anode on a substrate surface in a conventional manner. At this time, the substrate to be used is preferably a glass substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling and waterproofness. In addition, as a material for the anode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, may be used.

Next, a hole injection layer is formed on the anode surface by vacuum thermal evaporation or spin coating with a hole injection layer (HIL) material in a conventional manner. Materials for the hole injection layer include copper phthalocyanine (CuPc), 4,4',4"-tris(3-methylphenylamino)triphenylamine (m-MTDATA), 4,4',4"-tris(3-methylphenyl). Amino) phenoxybenzene (m-MTDAPB), starburst type amines 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), 4,4',4"-tris Examples include (N-(2-naphthyl)-N-phenylamino)-triphenylamine (2-TNATA) or IDE406 available from Idemitsu.

A hole transport layer (HTL) is formed on the surface of the hole injection layer by vacuum thermal evaporation or spin coating in a conventional manner. At this time, the material for the hole transport layer is bis(N-(1-naphthyl-n-phenyl))benzidine (α-NPD), N,N'-di(naphthalen-1-yl)-N,N'-biphenyl -Benzidine (NPB) or N,N'-biphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD) is exemplified.

An emission layer is formed by vacuum thermal evaporation or spin coating on the surface of the hole transport layer with an emission layer (EML) material in a conventional manner. At this time, as a single light-emitting material or a light-emitting host material among the light-emitting layer materials used, tris (8-hydroxyquinolinolato) aluminum (Alq ₃ ), etc. may be used for green, and Alq ₃ , CBP (4, 4'-N,N'-dicabazole-biphenyl, 4,4'-N,N'-dicarbazole-biphenyl), PVK(poly(n-vinylcabazole), poly(n-vinylcarbazole)), ADN( 9,10-di(naphthalene-2-yl)anthracene, 9,10-di(naphthalen-2-yl)anthracene), TCTA, TPBI(1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene , 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene), TBADN(3-tert-butyl-9,10-di(naphth-2-yl) anthracene, 3-tert-butyl -9,10-di (naphth-2 days) anthracene), E3, DSA (distyrylarylene, distyrylarylene), or a mixture of two or more thereof may be used, but the present invention is not limited thereto.

In the case of a dopant that can be used together with a light emitting host among the materials of the light emitting layer, the compound of the present invention may be preferably used.

Optionally, an electron blocking layer (EBL) may be additionally formed between the hole transport layer and the emission layer.

An electron transport layer is formed by vacuum thermal evaporation or spin coating of an electron transport layer (ETL) material on the surface of the light emitting layer in a conventional manner. At this time, the electron transport layer material to be used is not particularly limited, and preferably tris(8-hydroxyquinolinolato)aluminum (Alq ₃ ) may be used.

Optionally, by additionally forming a hole blocking layer (HBL) between the light emitting layer and the electron transport layer and using a phosphorescent dopant in the light emitting layer, it is possible to prevent the phenomenon that triplet excitons or holes are diffused into the electron transport layer. .

The hole blocking layer may be formed by vacuum thermal evaporation and spin coating on the hole blocking layer material in a conventional manner, and the hole blocking layer material is not particularly limited, but is preferably (8-hydroxyquinolinola). To) lithium (Liq), bis(8-hydroxy-2-methylquinolinolnato)-aluminum biphenoxide (BAlq), bathocuproine (BCP), and LiF may be used.

An electron injection layer is formed by vacuum thermal evaporation or spin coating on the surface of the electron transport layer with an electron injection layer (EIL) material in a conventional manner. In this case, materials such as LiF, Liq, Li ₂ O, BaO, NaCl, and CsF may be used as the electron injection layer material used.

A negative electrode is formed by vacuum thermal evaporation of a negative electrode material on the surface of the electron injection layer in a conventional manner.

At this time, the negative electrode materials used are lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), and magnesium-silver. (Mg-Ag) and the like can be used. In addition, in the case of a top emission organic electroluminescent device, indium tin oxide (ITO) or indium zinc oxide (IZO) may be used to form a transparent cathode through which light can pass.

A capping layer (CPL) may be formed on the surface of the negative electrode by the composition for forming a capping layer.

Hereinafter, a method for synthesizing the compounds will be described below with a representative example. However, the method for synthesizing the compounds of the present invention is not limited to the method illustrated below, and the compounds of the present invention may be prepared by the method illustrated below and a method known in the art.

[Synthesis Example 1: Preparation of Compound 55]

Starting material 1-1 compound 55

6.18 g (10 mmol) of the starting material 1-1 was dissolved in tert- Butylbenzene (42 ml), and then cooled to 0 °C. 11.8 ml (20 mmol) of 1.7 M tert- Butyllithium solution (in Pentane) was added under a nitrogen atmosphere, and the mixture was stirred at 60 to 70° C. for 2 hours. After that, the reaction was cooled to 0 °C again, and 1.93 mL (20 mmol) of Boron tribromide was added, followed by stirring at room temperature for 0.5 hours. The reaction was cooled to 0 °C again, 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added, followed by stirring at 60 °C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using Ethyl acetate and Water. The solvent of the extracted organic layer was dried over MgSO ₄ and then filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane). Thereafter, recrystallization and purification were performed with a DCM/Acetone mixed solvent to obtain 0.53 g of the compound 55 in 9% yield.

MS (MALDI-TOF) m/z: 592 [M]+

[Synthesis Example 2: Preparation of Compound 271]

Starting material 1-2 compound 271

Starting material 1-2 was dissolved in 5.02 g (10 mmol) tert- Butylbenzene (42 ml) and cooled to 0 °C. 11.8 ml (20 mmol) of 1.7 M tert- Butyllithium solution (in Pentane) was added under a nitrogen atmosphere, and the mixture was stirred at 60 to 70° C. for 2 hours.

After that, the reaction was cooled to 0 °C again, and 1.93 mL (20 mmol) of Boron tribromide was added, followed by stirring at room temperature for 0.5 hours. The reaction was cooled to 0 °C again, 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added, followed by stirring at 60 °C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using Ethyl acetate and Water. The solvent of the extracted organic layer was dried over MgSO ₄ and then filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane). Thereafter, recrystallization and purification were performed with a DCM/Acetone mixed solvent to obtain 0.52 g of compound 271 in an 11% yield.

MS (MALDI-TOF) m/z: 475 [M]+

[Synthesis Example 3: Preparation of Compound 270]

Starting material 1-3 compound 270

4.51 g (10 mmol) of the starting material 1-3 was dissolved in tert- Butylbenzene (42 ml), and then cooled to 0 °C. 11.8 ml (20 mmol) of 1.7 M tert- Butyllithium solution (in Pentane) was added under a nitrogen atmosphere, and the mixture was stirred at 60 to 70° C. for 2 hours.

Thereafter, the reaction mixture was cooled to 0°C, and 1.93 mL (20 mmol) of Boron tribromide was added, followed by stirring at room temperature for 0.5 hours. The reaction was cooled to 0 °C again, 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added, followed by stirring at 60 °C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using Ethyl acetate and Water. The solvent of the extracted organic layer was dried over MgSO ₄ and then filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane). Thereafter, recrystallization and purification were performed with a DCM/Acetone mixed solvent to obtain 0.6 g of the compound 270 in a 14% yield.

MS (MALDI-TOF) m/z: 425 [M]+

[Synthesis Example 4: Preparation of Compound 220]

Starting material 1-4 compound 220

After dissolving 7.0 g (10 mmol) of starting material 1-4 in tert- Butylbenzene (42 ml), it was cooled to 0 °C. 11.8 ml (20 mmol) of 1.7 M tert- Butyllithium solution (in Pentane) was added under a nitrogen atmosphere, and the mixture was stirred at 60 to 70° C. for 2 hours.

After that, the reaction was cooled to 0°C again, and 1.93 mL (20 mmol) of Boron tribromide was added, followed by stirring at room temperature for 0.5 hours. Again, the reaction was cooled to 0°C, 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added, followed by stirring at 60°C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using Ethyl acetate and Water. The solvent of the extracted organic layer was dried over MgSO ₄ and then filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane). Thereafter, recrystallization and purification were performed with a DCM/Acetone mixed solvent to obtain 0.67 g of the compound 220 in a 10% yield.

MS (MALDI-TOF) m/z: 673 [M]+

[Synthesis Example 5: Preparation of Compound 366]

Starting material 1-5 compound 366

Starting material 1-5 7.52 g (10 mmol) was dissolved in tert- butylbenzene (42 ml) and cooled to 0°C. In a nitrogen atmosphere, 2.5M n- butyllithium solution (in hexane) 8.0mL (20.0mmol) was added and stirred at room temperature for 3 hours.

After that, the reaction was cooled to 0°C again, and 1.90 mL (20.0 mmol) of Boron tribromide was added, followed by stirring at room temperature for 0.5 hours. The reaction was cooled to 0°C again, 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added, followed by stirring at 70°C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using Ethyl acetate and Water. The solvent of the extracted organic layer was dried over MgSO ₄ and then filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane).

Thereafter, recrystallization and purification were performed with a DCM/Acetone mixed solvent to obtain 0.94 g of the compound 366 in a 13% yield.

MS (MALDI-TOF) m/z: 725 [M]+

[Synthesis Example 6: Preparation of Compound 156]

Starting material 1-6 compound 156

7.59 g (10 mmol) of the starting material 1-6 was dissolved in tert- butylbenzene (42 ml) and cooled to 0 °C. In a nitrogen atmosphere, 2.5M n- butyllithium solution (in hexane) 8.0mL (20.0mmol) was added and stirred at room temperature for 3 hours.

After that, the reaction was cooled to 0°C again, and 1.90 mL (20.0 mmol) of Boron tribromide was added, followed by stirring at room temperature for 0.5 hours. The reaction was cooled to 0°C again, 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added, followed by stirring at 70°C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using Ethyl acetate and Water. The solvent of the extracted organic layer was dried over MgSO ₄ and then filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane).

After recrystallization and purification with a DCM/Acetone mixed solvent, 1.10 g of Compound 156 was obtained in a 15% yield.

MS (MALDI-TOF) m/z: 704 [M]+

[Synthesis Example 7: Preparation of Compound 263]

Starting material 1-7 compound 263

Starting material 1-7 9.06 g (10 mmol) was dissolved in tert- butylbenzene (42 ml) and then cooled to 0 °C. In a nitrogen atmosphere, 2.5M n- butyllithium solution (in hexane) 8.0mL (20.0mmol) was added and stirred at room temperature for 3 hours.

After that, the reaction was cooled to 0°C again, and 1.90 mL (20.0 mmol) of Boron tribromide was added, followed by stirring at room temperature for 0.5 hours. The reaction was cooled to 0°C again, 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added, followed by stirring at 70°C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using Ethyl acetate and Water. The solvent of the extracted organic layer was dried over MgSO ₄ and then filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane).

Thereafter, recrystallization and purification were performed with a DCM/Acetone mixed solvent to obtain 0.44 g of the compound 263 in 5% yield.

MS (MALDI-TOF) m/z: 880 [M]+

[Synthesis Example 8: Preparation of Compound 187]

Starting material 1-8 compound 187

Starting material 1-8 7.40 g (10 mmol) was dissolved in tert- butylbenzene (42 ml), and then cooled to 0°C. In a nitrogen atmosphere, 2.5M n- butyllithium solution (in hexane) 8.0mL (20.0mmol) was added and stirred at room temperature for 3 hours.

After that, the reaction was cooled to 0°C again, and 1.90 mL (20.0 mmol) of Boron tribromide was added, followed by stirring at room temperature for 0.5 hours. The reaction was cooled to 0°C again, 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added, followed by stirring at 70°C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using Ethyl acetate and Water. The solvent of the extracted organic layer was dried over MgSO ₄ and then filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane).

Thereafter, recrystallization and purification were performed with a DCM/Acetone mixed solvent to obtain 0.74 g of the compound 187 in a 10% yield.

MS (MALDI-TOF) m/z: 638 [M]+

[Synthesis Example 9: Preparation of Compound 367]

Starting material 1-9 compound 367

7.27 g (10 mmol) of the starting material 1-9 was dissolved in tert- butylbenzene (42 ml) and cooled to 0 °C. In a nitrogen atmosphere, 2.5M n- butyllithium solution (in hexane) 8.0mL (20.0mmol) was added and stirred at room temperature for 3 hours.

After that, the reaction was cooled to 0°C again, and 1.90 mL (20.0 mmol) of Boron tribromide was added, followed by stirring at room temperature for 0.5 hours. The reaction was cooled to 0°C again, 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added, followed by stirring at 70°C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using Ethyl acetate and Water. The solvent of the extracted organic layer was dried over MgSO ₄ and then filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane).

Thereafter, recrystallization and purification were performed with a DCM/Acetone mixed solvent to obtain 0.49 g of the compound 367 in a 7% yield.

MS (MALDI-TOF) m/z: 700 [M]+

[Synthesis Example 10: Preparation of Compound 368]

Starting material 1-10 compound 368

Starting material 1-10 8.31 g (10 mmol) was dissolved in tert- butylbenzene (42 ml), and then cooled to 0 °C. In a nitrogen atmosphere, 2.5M n- butyllithium solution (in hexane) 8.0mL (20.0mmol) was added and stirred at room temperature for 3 hours.

After that, the reaction was cooled to 0°C again, and 1.90 mL (20.0 mmol) of Boron tribromide was added, followed by stirring at room temperature for 0.5 hours. The reaction was cooled to 0°C again, 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added, followed by stirring at 70°C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using Ethyl acetate and Water. The solvent of the extracted organic layer was dried over MgSO ₄ and then filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane).

Thereafter, recrystallization and purification were performed with a DCM/Acetone mixed solvent to obtain 0.88 g of Compound 368 in 11% yield.

MS (MALDI-TOF) m/z: 654 [M]+

[Synthesis Example 11: Preparation of Compound 338]

Starting material 1-11 compound 338

5.72 g (10 mmol) of the starting material 1-11 was dissolved in tert- Butylbenzene (42 ml), and then cooled to 0 °C. 11.8 ml (20 mmol) of 1.7 M tert- Butyllithium solution (in Pentane) was added under a nitrogen atmosphere, and the mixture was stirred at 60 to 70° C. for 2 hours. After that, the reaction was cooled to 0°C again, and 1.90 mL (20 mmol) of Boron tribromide was added, followed by stirring at room temperature for 0.5 hours. The reaction was cooled to 0 °C again, 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added, followed by stirring at 60 °C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using Ethyl acetate and Water. The solvent of the extracted organic layer was dried over MgSO ₄ and then filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane). Thereafter, recrystallization and purification were performed with a DCM/Acetone mixed solvent to obtain 0.44 g of the compound 338 in an 8% yield.

MS (MALDI-TOF) m/z: 546 [M]+

[Synthesis Example 12: Preparation of Compound 369]

Starting material 1-12 compound 369

After dissolving 6.54 g (10 mmol) of starting material 1-12 in tert- butylbenzene (42 ml), it was cooled to 0°C. In a nitrogen atmosphere, 2.5M n- butyllithium solution (in hexane) 8.0mL (20.0mmol) was added and stirred at room temperature for 3 hours.

After that, the reaction was cooled to 0°C again, and 1.90 mL (20.0 mmol) of Boron tribromide was added, followed by stirring at room temperature for 0.5 hours. The reaction was cooled to 0°C again, 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added, followed by stirring at 70°C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using Ethyl acetate and Water. The solvent of the extracted organic layer was dried over MgSO ₄ and then filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane).

Thereafter, recrystallization and purification were performed with a DCM/Acetone mixed solvent to obtain 1.0 g of compound 369 in a 16% yield.

MS (MALDI-TOF) m/z: 627 [M]+

[Synthesis Example 1-13: Preparation of Compound 61]

Starting material 1-13 compound 61

7.97 g (10 mmol) of the starting material 1-13 was dissolved in tert- butylbenzene (42 ml) and then cooled to 0 °C. In a nitrogen atmosphere, 2.5M n- butyllithium solution (in hexane) 8.0mL (20.0mmol) was added and stirred at room temperature for 3 hours.

After that, the reaction was cooled to 0°C again, and 1.90 mL (20.0 mmol) of Boron tribromide was added, followed by stirring at room temperature for 0.5 hours. The reaction was cooled to 0°C again, 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added, followed by stirring at 70°C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using Ethyl acetate and Water. The solvent of the extracted organic layer was dried over MgSO ₄ and then filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane).

Thereafter, recrystallization and purification were performed with a DCM/Acetone mixed solvent to obtain 0.65 g of Compound 61 in 9% yield.

MS (MALDI-TOF) m/z: 726 [M]+

[Synthesis Example 1-14: Preparation of Compound 76]

Starting material 1-14 compound 76

After dissolving 8.43 g (10 mmol) of the starting material 1-14 in tert- Butylbenzene (42 ml), it was cooled to 0 °C. 11.8 ml (20 mmol) of 1.7 M tert- Butyllithium solution (in Pentane) was added under a nitrogen atmosphere, and the mixture was stirred at 60 to 70° C. for 2 hours. After that, the reaction was cooled to 0 °C again, and 1.90 mL (20 mmol) of Boron tribromide was added, followed by stirring at room temperature for 0.5 hours. The reaction was cooled to 0 °C again, 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added, followed by stirring at 60 °C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using Ethyl acetate and Water. The solvent of the extracted organic layer was dried over MgSO ₄ and then filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane). Thereafter, recrystallization and purification were performed with a DCM/Acetone mixed solvent to obtain 0.82 g of compound 76 in a 10% yield.

MS (MALDI-TOF) m/z: 816 [M]+

[Synthesis Example 1-15: Preparation of Compound 75]

Starting material 1-15 compound 75

Starting material 1-15 7.97 g (10 mmol) was dissolved in tert- butylbenzene (42 ml), and then cooled to 0 °C. In a nitrogen atmosphere, 2.5M n- butyllithium solution (in hexane) 8.0mL (20.0mmol) was added and stirred at room temperature for 3 hours.

After that, the reaction was cooled to 0°C again, and 1.90 mL (20.0 mmol) of Boron tribromide was added, followed by stirring at room temperature for 0.5 hours. The reaction was cooled to 0°C again, 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added, followed by stirring at 70°C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using Ethyl acetate and Water. The solvent of the extracted organic layer was dried over MgSO ₄ and then filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane).

Thereafter, recrystallization and purification were performed with a DCM/Acetone mixed solvent to obtain 1.04 g of the compound 75 in a 13% yield.

MS (MALDI-TOF) m/z: 799 [M]+

<Example 1: Method for manufacturing an organic electroluminescent device with a rear light emitting structure>

The substrate on which ITO (100nm), which is the anode of the organic electroluminescent device, was stacked, was patterned by dividing it into a cathode, an anode region, and an insulating layer through a photo-lithograph process, and then the work function of the anode (ITO) ( The surface was treated with UV Ozone treatment and O ₂ :N ₂ plasma for the purpose of increasing work-function and cleaning. A hole injection layer (HIL) was formed thereon to a thickness of 10 nm. Then, on the hole injection layer, a hole transport layer was vacuum deposited to have a thickness of 90 nm, and an electron blocking layer (EBL) was formed on the hole transport layer (HTL) to a thickness of 10 nm. A host of the emission layer was deposited on the electron blocking layer (EBL) and at the same time, 2% of Compound 55 was doped with a dopant to form an emission layer (EML) with a thickness of 25 nm.

An electron transport layer (ETL) was deposited thereon by 25 nm, an electron injection layer was deposited on the electron transport layer by 1 nm, and aluminum was deposited as a cathode to a thickness of 100 nm. Thereafter, an organic electroluminescent device was manufactured by bonding a seal cap including a getter with a UV-curable adhesive to protect the organic electroluminescent device from oxygen or moisture in the atmosphere.

<Examples 2 to 14: Preparation of organic electroluminescent device>

Organic electric field using the same method as in Example 1, except that Compounds 61, 75, 76, 271, 270, 220, 366, 156, 263, 187, 367, 338, 369 were used instead of Compound 55 as a dopant. A light emitting device was manufactured.

<Comparative Example 1: Fabrication of organic electroluminescent device>

An organic electroluminescent device was manufactured using the same method as in Example 1, except that Compound A was used instead of Compound 55 as a dopant.

<Compound A>

<Characteristic analysis of organic light emitting device>

The following is a result of measuring the electroluminescence characteristics by applying a current of 10 mA/cm ² to the organic electroluminescent device of the rear light emitting structure prepared in Examples 1 to 14 and Comparative Example 1, and measuring the lifetime by driving a constant current of 40 mA/cm ² . It compared with Table 1 and shown.

division DOPANT Voltage(V) Current efficiency
(Cd/A) Color characteristics life span
T95
(hr) CIE x CIE y Example 1 Compound 55 4.00 6.5 0.129 0.097 95 Example 2 Compound 61 4.02 5.6 0.128 0.106 100 Example 3 Compound 75 3.93 8.6 0.1238 0.1102 75 Example 4 Compound 76 3.97 8.2 0.1241 0.1080 110 Example 5 Compound 271 3.86 4.9 0.14 0.059 70 Example 6 Compound 270 3.85 5.2 0.139 0.059 75 Example 7 Compound 220 3.96 7.4 0.113 0.118 85 Example 8 Compound 366 3.97 6.7 0.129 0.095 80 Example 9 Compound 156 3.91 7.78 0.114 0.115 72 Example 10 Compound 263 3.78 5.0 0.1166 0.136 86 Example 11 Compound 187 3.83 6.1 0.1155 0.1404 70 Example 12 Compound 367 3.84 6.1 0.1144 0.1455 78 Example 13 Compound 338 3.94 6.9 0.114 0.114 95 Example 14 Compound 369 4.04 6.4 0.1284 0.100 80 Comparative Example 1 Compound A 4.10 4.4 0.1387 0.0635 45

According to the above experimental results, compared to Comparative Example 1, when the compound of the Example of the present invention was used, an organic compound having excellent efficiency and electrochemical stability was used, and the driving voltage was low, the color characteristics were excellent, and the characteristics such as long life. This excellent organic electroluminescent device can be provided.

Although the preferred embodiments of the present invention have been described in detail above, the scope of the present invention is not limited thereto, and various modifications and improvements by those skilled in the art using the basic concept of the present invention defined in the following claims are also present. It belongs to the scope of rights of

Claims (8)

A multimer comprising the structure of a compound represented by the following formula 1 or 2, or a compound represented by the following formula 1 or 2
compound:
[Formula 1]

[Formula 2]

here,
n is an integer from 0 to 2,
a to f are the same as or different from each other, each independently an integer of 0 or 1, a + b + c + d

Is 1,
e + f

Is 1,
Y ₁ and Y ₂ are the same as or different from each other, and each independently B, N, P=O or P=S,
Rings A to G are the same or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms,
X ₁ to X ₃ are the same as or different from each other, and each independently B, N, O, S, Se or Si,
X ₄ is B, O, S, NR ₃ , Si(R ₄ )(R ₅ ) or Se,
Z ₁ to Z ₆ are the same as or different from each other, and each independently Si(R ₆ )(R ₇ ), B(R ₈ ), N(R ₉ ), a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, It is selected from the group consisting of a substituted or unsubstituted alkenylene group having 2 to 10 carbon atoms and a substituted or unsubstituted arylene group having 6 to 30 carbon atoms,
R ₁ to R ₉ are the same as or different from each other, and each independently hydrogen, a cyano group, a trifluoromethyl group, a nitro group, a halogen group, a hydroxy group, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, A substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C20 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C24 alkynyl group , Substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, substituted or unsubstituted 6 to 30 carbon atoms Heteroarylalkyl group, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, substituted or unsubstituted carbon number 6 to 30 aralkylamino group, substituted or unsubstituted C2-C24 hetero arylamino group, substituted or unsubstituted C1-C30 alkylsilyl group, substituted or unsubstituted C6-C30 arylsilyl group, and It is selected from the group consisting of a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and may be bonded to each other with adjacent groups to form a substituted or unsubstituted ring,
When A to G, Z ₁ to Z ₆ and R ₁ to R ₉ are substituted, hydrogen, cyano group, trifluoromethyl group, nitro group, halogen group, hydroxy group, alkylthio group having 1 to 4 carbon atoms, 1 carbon number Alkyl group of to 30, cycloalkyl group of 1 to 20 carbon atoms, alkenyl group of 2 to 30 carbon atoms, alkynyl group of 2 to 24 carbon atoms, aralkyl group of 7 to 30 carbon atoms, aryl group of 6 to 30 carbon atoms, 2 to 60 carbon atoms Heteroaryl group, heteroarylalkyl group having 6 to 30 carbon atoms, alkoxy group having 1 to 30 carbon atoms, alkylamino group having 1 to 30 carbon atoms, arylamino group having 6 to 30 carbon atoms, aralkylamino group having 6 to 30 carbon atoms, 2 to 24 carbon atoms Is substituted with a substituent selected from the group consisting of a heteroarylamino group, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms, and is bonded to adjacent groups to be substituted or provided A cyclic ring may be formed, and when substituted with a plurality of substituents, they are the same as or different from each other. The method of claim 1,
The rings A to G are the same or different from each other, and each independently a substituted or unsubstituted aryl group having 5 to 15 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms
compound. The method of claim 1,
Wherein Y ₁ and Y ₂ are B
compound. The method of claim 1,
The X ₁ to X ₃ are the same as or different from each other, and each independently N or O
compound. A first electrode; A second electrode provided opposite to the first electrode; And an organic material layer of at least one layer provided between the first electrode and the second electrode,
At least one of the one or more organic material layers comprises the compound according to claim 1
Organic electroluminescent device. The method of claim 5,
The organic material layer is selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
Organic electroluminescent device. The method of claim 5,
The organic material layer is an organic electroluminescent device that is an emission layer. The method of claim 5,
The organic material layer is an organic electroluminescent device comprising a hole injection layer, a hole transport layer, or an electron blocking layer.